Organic photoconductive materials that are developed as photosensitive materials or hole transport materials have many advantages such as low costs, variable processability, and non-pollution, and many compounds are proposed. For example, there are disclosed materials such as oxadiazole derivatives (for example, see Patent Document 1), oxazole derivatives (for example, see Patent Document 2), hydrazone derivatives (for example, see Patent Document 3), triarylpyrazoline derivatives (for example, see Patent Documents 4 and 5), arylamine derivatives (for example, see Patent Documents 6 and 7), and stilbene derivatives (for example, see Patent Documents 8 and 9).
Above all, arylamine derivatives such as 4,4′,4″-tris[N,N-(1-naphthyl)phenylamino]triphenylamine (1-TNATA), 4,4′,4″-tris[N,N-(m-tolyl)phenylamino]triphenylamine (MTDATA), 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (α-NPD), and 4,4′-bis[N-(m-tolyl)-N-phenylamino]biphenyl (TPD) are largely used as hole transport or hole injection materials (for example, see Non-Patent Documents 1 and 2).
Recently, many fluorene derivatives are developed (for example, see Patent Documents 10, 11, 12, 13, 14 and 16).
However, those materials have drawbacks such as poor stability and poor durability. For example, because a-NPD is originally a crystalline compound, a-NPD thin film formed by vacuum deposition causes crystallization or cohesion when it is allowed to stand for about 2 weeks. As a result, the thin film becomes white turbid. Further, 2,7-bis(dinaphthylamino)-9,9-dimethylfluorene in which 9,9-positions are dimethyl groups (for example, see Patent Document 11) and 2,7-bis(N,N-diphenylamino)-9,9-diphenylfluorene in which 9,9-positions are diphenyl groups (for example, see Patent Document 16), that are representative fluorene derivatives, also have high crystallinity, and therefore have the same problems as above. As a result, in the case of utilizing to organic thin film devices such as organic EL devices, there is the problem that the possibility of causing short, dark spot or the like is large. At present, development of hole transport materials having an excellent hole transport capability, an excellent thin film stability and high Tg (glass transition temperature) is desired. Further, as a process of producing arylamines, there is known a method of using a catalyst comprising trialkylphosphines and a palladium compound in the amination reaction of aryl halides by an amine compound in the presence of a base (for example, see Patent Document 15).    Patent Document 1
U.S. Pat. No. 3,189,447 (Claims)    Patent Document 2
U.S. Pat. No. 3,257,203 (Claims)    Patent Document 3
JP-A-54-59143 (Claims)    Patent Document 4
JP-A-51-93224 (Claims)    Patent Document 5
JP-A-55-108667 (Claims)    Patent Document 6
JP-A-55-144250 (Claims)    Patent Document 7
JP-A-56-119132 (Claims)    Patent Document 8
JP-A-58-190953 (Claims)    Patent Document 9
JP-A-59-195658 (Claims)    Patent Document 10
JP-A-11-35532 (Claims)    Patent Document 11
JP-A-12-16973 (Claims)    Patent Document 12
JP-A-12-302756 (Claims)    Patent Document 13
JP-A-12-327638 (Claims)    Patent Document 14
JP-A-13-39933 (Claims)    Patent Document 15
JP-A-10-139742 (Claims)
Patent Document 16
JP-A-10-95972 (Claims)    Non-Patent Document 1
Advanced Materials, (Germany), 1998, Vol. 10, No. 14, pp. 1108-1112 (FIG. 1 and Table 1)    Non-Patent Document 2
Journal of Luminescence, (Holland), 1997, 72-74, pp. 985-991 (FIG. 1)